Title: Atisine
CAS Registry Number: 466-43-3
Additional Names: Anthorine
Molecular Formula: C22H33NO2
Molecular Weight: 343.50
Percent Composition: C 76.92%, H 9.68%, N 4.08%, O 9.32%
Literature References: From roots of the "atis" plant, Aconitum heterophyllum Wall., and from A. anthora L., Ranunculaceae: Broughton, Blue Book of East India Cinchona Cultivation 1877, 133; Goris, Metin, Compt. Rend. 180, 968 (1925); Lawson, Topps, J. Chem. Soc. 1937, 1640. Structure: Wiesner et al., Chem. Ind. (London) 1954, 132; Pelletier, Jacobs, J. Am. Chem. Soc. 76, 4496 (1954). Structure and stereochemistry: Dvornik, Edwards, Can. J. Chem. 42, 137 (1964). Partial synthesis: Pelletier, Jacobs, J. Am. Chem. Soc. 78, 4144 (1956); Pelletier, Parthasarathy, Tetrahedron Lett. 1963, 205. Racemic synthesis and resolution: Nagata et al., J. Am. Chem. Soc. 85, 2342 (1963); 89, 1499 (1967); Masamune, ibid. 86, 291 (1964); Guthrie et al., Tetrahedron Lett. 1966, 4645. 13C-NMR study of C-20 epimers: N. V. Mody, S. W. Pelletier, Tetrahedron 34, 2421 (1978).
Properties: Solid, mp 57-60°. Distills in high vacuum at a bath temp of 140°. Strong base: pK 12.2.
Melting point: mp 57-60°
pKa: pK 12.2
Derivative Type: Hydrochloride
Molecular Formula: C22H33NO2.HCl
Molecular Weight: 379.96
Percent Composition: C 69.54%, H 9.02%, N 3.69%, O 8.42%, Cl 9.33%
Properties: Flat needles from dil alc, dec 311-312°. [a]D25 +28°.
Optical Rotation: [a]D25 +28°
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